ES2224652T3 - Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos. - Google Patents

Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos.

Info

Publication number: ES2224652T3
Authority: ES; Spain
Prior art keywords: phenyl; alkyl; substituted; ethyl; hydrogen
Prior art date: 1998-04-17
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES99920661T

Other languages

English (en)

Spanish (es)

Inventor

Michael Brenner

Wolf-Dietrich Bechtel

Rainer Palluk

Marion Wienrich

Thomas Weiser

Enzo Cereda

Maura Bignotti

Carlomaria Pellegrini

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Boehringer Ingelheim Pharma GmbH and Co KG

Boehringer Ingelheim Italia SpA

Boehringer Ingelheim Pharmaceuticals Inc

Original Assignee

Boehringer Ingelheim Pharma GmbH and Co KG

Boehringer Ingelheim Italia SpA

Boehringer Ingelheim Pharmaceuticals Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-04-17

Filing date

1999-04-14

Publication date

2005-03-01

1999-04-14 Application filed by Boehringer Ingelheim Pharma GmbH and Co KG, Boehringer Ingelheim Italia SpA, Boehringer Ingelheim Pharmaceuticals Inc filed Critical Boehringer Ingelheim Pharma GmbH and Co KG

2005-03-01 Application granted granted Critical

2005-03-01 Publication of ES2224652T3 publication Critical patent/ES2224652T3/es

2019-04-14 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 8
239000003814 drug Substances 0.000 title claims description 5
229940079593 drug Drugs 0.000 title claims description 5
-1 triazoline Chemical compound 0.000 claims abstract description 67
239000000203 mixture Substances 0.000 claims abstract description 64
239000001257 hydrogen Substances 0.000 claims abstract description 63
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
150000001875 compounds Chemical class 0.000 claims abstract description 43
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 42
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 36
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 33
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 31
239000000460 chlorine Substances 0.000 claims abstract description 31
229910052801 chlorine Inorganic materials 0.000 claims abstract description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 28
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 27
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 27
229910052794 bromium Inorganic materials 0.000 claims abstract description 27
150000002431 hydrogen Chemical class 0.000 claims abstract description 27
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 24
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 22
239000011737 fluorine Substances 0.000 claims abstract description 22
229910052731 fluorine Inorganic materials 0.000 claims abstract description 22
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 18
229910052760 oxygen Inorganic materials 0.000 claims abstract description 18
239000001301 oxygen Substances 0.000 claims abstract description 18
150000007513 acids Chemical class 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 17
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims abstract description 16
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 15
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 14
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims abstract description 12
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 12
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims abstract description 12
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims abstract description 9
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 9
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 9
150000003852 triazoles Chemical class 0.000 claims abstract description 9
RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 claims abstract description 8
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims abstract description 8
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims abstract description 8
ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 7
229920006395 saturated elastomer Polymers 0.000 claims abstract description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
UUZJJNBYJDFQHL-UHFFFAOYSA-N 1,2,3-triazolidine Chemical compound C1CNNN1 UUZJJNBYJDFQHL-UHFFFAOYSA-N 0.000 claims abstract description 5
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims abstract description 5
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims abstract description 5
WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims abstract description 5
150000001204 N-oxides Chemical class 0.000 claims abstract description 5
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims abstract description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
125000005842 heteroatom Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 38
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
150000003254 radicals Chemical class 0.000 claims description 19
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 18
239000013543 active substance Substances 0.000 claims description 15
239000000126 substance Substances 0.000 claims description 14
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 6
239000002671 adjuvant Substances 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
JKNSMBZZZFGYCB-UHFFFAOYSA-N 4,5-dihydrooxadiazole Chemical compound C1CN=NO1 JKNSMBZZZFGYCB-UHFFFAOYSA-N 0.000 claims description 4
201000006474 Brain Ischemia Diseases 0.000 claims description 4
206010008120 Cerebral ischaemia Diseases 0.000 claims description 4
206010008118 cerebral infarction Diseases 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
208000015122 neurodegenerative disease Diseases 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
239000012039 electrophile Substances 0.000 claims description 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
229910006069 SO3H Inorganic materials 0.000 abstract 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
239000000243 solution Substances 0.000 description 76
239000002904 solvent Substances 0.000 description 68
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
238000003756 stirring Methods 0.000 description 39
239000012074 organic phase Substances 0.000 description 37
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 34
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
238000000746 purification Methods 0.000 description 27
238000005292 vacuum distillation Methods 0.000 description 25
238000010992 reflux Methods 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
239000003921 oil Substances 0.000 description 20
235000019198 oils Nutrition 0.000 description 20
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000011734 sodium Substances 0.000 description 18
238000001816 cooling Methods 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 16
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
238000001035 drying Methods 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000008346 aqueous phase Substances 0.000 description 12
239000012071 phase Substances 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000004821 distillation Methods 0.000 description 10
238000000605 extraction Methods 0.000 description 10
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
229910052708 sodium Inorganic materials 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 9
239000000047 product Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000008101 lactose Substances 0.000 description 7
239000008107 starch Substances 0.000 description 7
235000019698 starch Nutrition 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000013078 crystal Substances 0.000 description 6
229910052736 halogen Inorganic materials 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
206010021143 Hypoxia Diseases 0.000 description 5
239000007832 Na2SO4 Substances 0.000 description 5
239000012230 colorless oil Substances 0.000 description 5
239000008120 corn starch Substances 0.000 description 5
229940099112 cornstarch Drugs 0.000 description 5
239000000499 gel Substances 0.000 description 5
239000001267 polyvinylpyrrolidone Substances 0.000 description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
238000000926 separation method Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
SFOGMHGZRYIHFL-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-phenylpyrrole Chemical compound COC1=CC=CC=C1N1C=C(C=2C=CC=CC=2)C=C1 SFOGMHGZRYIHFL-UHFFFAOYSA-N 0.000 description 4
ZJABPUSDYOXUKS-UHFFFAOYSA-N 1-(2-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ZJABPUSDYOXUKS-UHFFFAOYSA-N 0.000 description 4
PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 4
ZGGUPHZEVASDAF-UHFFFAOYSA-N 5-(2-methoxyphenyl)-3-phenyl-1,3,4-oxadiazol-2-one Chemical compound COC1=CC=CC=C1C(OC1=O)=NN1C1=CC=CC=C1 ZGGUPHZEVASDAF-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000003282 alkyl amino group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000004663 dialkyl amino group Chemical group 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000001802 infusion Methods 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000454 talc Substances 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
ZWTRSTWJBWJEFR-VAWYXSNFSA-N (e)-3-(2-methoxyphenyl)-1-phenylprop-2-en-1-one Chemical compound COC1=CC=CC=C1\C=C\C(=O)C1=CC=CC=C1 ZWTRSTWJBWJEFR-VAWYXSNFSA-N 0.000 description 3
ZYDSBZHDRVWPKC-UHFFFAOYSA-N 1-(2-methoxyphenyl)-3-phenyl-1,2,4-triazole Chemical compound COC1=CC=CC=C1N1N=C(C=2C=CC=CC=2)N=C1 ZYDSBZHDRVWPKC-UHFFFAOYSA-N 0.000 description 3
NAHBHGCMMCYATQ-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-phenylpyrrole-2,3-dicarboxylic acid Chemical compound COC1=CC=CC=C1N1C(C(O)=O)=C(C(O)=O)C(C=2C=CC=CC=2)=C1 NAHBHGCMMCYATQ-UHFFFAOYSA-N 0.000 description 3
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239000008215 water for injection Substances 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/333—Radicals substituted by oxygen or sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
- C07D231/22—One oxygen atom attached in position 3 or 5 with aryl radicals attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyrrole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

ES99920661T 1998-04-17 1999-04-14 Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos. Expired - Lifetime ES2224652T3 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19816880A DE19816880A1 (de)	1998-04-17	1998-04-17	Neue Diphenyl-substituierte 5-Ring-Heterocyclen, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel
ITMI980818		1998-04-17
IT98MI000818A IT1300055B1 (it)	1998-04-17	1998-04-17	Eterocicli con anello a 5 termini difenil-sostituiti loro procedimento di preparazione e loro impiego come farmici
DE19816880		1998-04-17

Publications (1)

Publication Number	Publication Date
ES2224652T3 true ES2224652T3 (es)	2005-03-01

Family

ID=26045525

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES99920661T Expired - Lifetime ES2224652T3 (es)	1998-04-17	1999-04-14	Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos.

Country Status (10)

Country	Link
US (1)	US6255327B1 (de)
EP (1)	EP1071670B1 (de)
JP (1)	JP4589531B2 (de)
AT (1)	ATE270665T1 (de)
CA (1)	CA2322195C (de)
DE (2)	DE19816880A1 (de)
ES (1)	ES2224652T3 (de)
IT (1)	IT1300055B1 (de)
MX (1)	MXPA00009474A (de)
WO (1)	WO1999054314A1 (de)

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ATE257827T1 (de)	1999-07-21	2004-01-15	Hoffmann La Roche	Triazolderivate
US6579880B2 (en) *	2000-06-06	2003-06-17	Ortho-Mcneil Pharmaceutical, Inc.	Isoxazoles and oxadiazoles as anti-inflammatory inhibitors of IL-8
US6610723B2 (en) *	2001-01-29	2003-08-26	Hoffmann-La Roche Inc.	Imidazole derivatives
US8829198B2 (en) *	2007-10-31	2014-09-09	Proteotech Inc	Compounds, compositions and methods for the treatment of beta-amyloid diseases and synucleinopathies
GB0303503D0 (en) *	2003-02-14	2003-03-19	Novartis Ag	Organic compounds
CN1922156A (zh) *	2003-11-10	2007-02-28	默克公司	作为钠通道阻断剂的取代的三唑
US20070191448A1 (en) *	2004-03-08	2007-08-16	Robert Zelle	Ion channel modulators
DOP2005000123A (es) *	2004-07-02	2011-07-15	Merck Sharp & Dohme	Inhibidores de cetp
EP2402323A3 (de)	2004-10-13	2012-05-30	PTC Therapeutics, Inc.	Pyrazol- oder Triazolverbindungen und ihre Verwendung zur Herstellung eines Heilmittels zur Behandlung durch somatische Mutationen bewirkter Krankheiten
US20110158907A1 (en) *	2007-04-19	2011-06-30	The Trustees Of The Univeristy Of Pennsylvania	Diphenyl-heteroaryl derivatives and their use for binding and imaging amyloid plaques
WO2009111611A2 (en)	2008-03-05	2009-09-11	Proteotech Inc.	Compounds, compositions and methods for the treatment of islet amyloid polypeptide (iapp) accumulation in diabetes
CN102060798A (zh) *	2011-01-04	2011-05-18	复旦大学	2-(1-氢-4-四唑)-4′- 甲基联苯及其衍生物的合成方法
WO2012118935A1 (en)	2011-03-03	2012-09-07	Proteotech Inc	Compounds for the treatment of neurodegenerative diseases
MA52033A (fr) *	2014-08-13	2021-01-20	Nippon Soda Co	Composé de diarylimidazole et agent de lutte antiparasitaire

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FR5305E (fr) *	1905-06-17	1906-02-22	Edouard Pellorce	Appareil électrique pour l'allumage des moteurs à explosion
DE1545806A1 (de) *	1951-01-28	1969-11-27	Hoechst Ag	Verfahren zur Herstellung von heterocyclischen Verbindungen
FR1356901A (fr) *	1958-03-13	1964-04-03		Nouveaux aminoétheroxydes, aminothioéthers et aminoesters dérivés du pyrrole, etleur procédé de préparation
FR2152345A1 (en) *	1971-09-06	1973-04-27	Roussel Uclaf	Alpha-(2-thiazolyl)oxyalkanoic acids and derivatives - - with analgesic,antiinflammatory and antipyretic activity
FR2244462A1 (en) *	1973-09-25	1975-04-18	Delalande Sa	Antihypertensive, 5-hydroxy methyl 1,2,4-triazoles - prepd. from aniline and a hydroxy methyl 1,3,4-oxadiazole
SU753084A1 (ru) *	1979-03-23	1983-01-23	Ростовский Ордена Трудового Красного Знамени Государственный Университет	Способ получени 1-[2-алкил(аралкил)аминоарил -4-арилимидазолов общей формулы
US4370336A (en) *	1979-06-11	1983-01-25	Gruppo Lepetit S.P.A.	3,5-Disubstituted-1H-1,2,4-triazole derivatives as antifertility agents
US4379155A (en) *	1979-06-11	1983-04-05	Gruppo Lepetit S.P.A.	3,5-Disubstituted-1H-1,2,4-triazole derivatives
US4826868A (en) *	1986-05-29	1989-05-02	Ortho Pharmaceutical Corporation	1,5-Diaryl-3-substituted pyrazoles pharmaceutical compositions and use
JP2928307B2 (ja) *	1989-02-03	1999-08-03	エーザイ株式会社	ピロリジン誘導体
CA2074933C (en) *	1990-11-30	2002-12-03	Masatoshi Chihiro	Thiazole derivatives as active superoxide radical inhibitors
FR2678938B1 (fr) *	1991-07-10	1993-10-08	Rhone Poulenc Rorer Sa	Derives de pyrrolidine, leur preparation et les medicaments les contenant.
IL104311A (en) *	1992-02-05	1997-07-13	Fujisawa Pharmaceutical Co	Pyrazole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same
US5411977A (en) *	1993-03-31	1995-05-02	The Dupont Merck Pharmaceutical Company	Substituted 2,5-diaryl-4-isothiazolin-3-ones as antiinflammatory and antithrombotic agents
DE19528189A1 (de) *	1995-08-01	1997-02-06	Basf Ag	Benzolderivate mit einem heterocyclischen Rest
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DE19643037A1 (de)	1996-10-18	1998-04-23	Boehringer Ingelheim Kg	Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel
EP0946587A2 (de) *	1996-12-16	1999-10-06	Fujisawa Pharmaceutical Co., Ltd.	Amindverbindungen und ihre verwendung als inhibitoren der bitric-oxid-synthase

1998
- 1998-04-17 DE DE19816880A patent/DE19816880A1/de not_active Withdrawn
- 1998-04-17 IT IT98MI000818A patent/IT1300055B1/it active IP Right Grant
1999
- 1999-04-13 US US09/290,931 patent/US6255327B1/en not_active Expired - Lifetime
- 1999-04-14 AT AT99920661T patent/ATE270665T1/de active
- 1999-04-14 WO PCT/EP1999/002496 patent/WO1999054314A1/de not_active Ceased
- 1999-04-14 DE DE59909917T patent/DE59909917D1/de not_active Expired - Lifetime
- 1999-04-14 JP JP2000544653A patent/JP4589531B2/ja not_active Expired - Fee Related
- 1999-04-14 ES ES99920661T patent/ES2224652T3/es not_active Expired - Lifetime
- 1999-04-14 EP EP99920661A patent/EP1071670B1/de not_active Expired - Lifetime
- 1999-04-14 MX MXPA00009474A patent/MXPA00009474A/es active IP Right Grant
- 1999-04-14 CA CA002322195A patent/CA2322195C/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2002512235A (ja)	2002-04-23
CA2322195A1 (en)	1999-10-28
DE19816880A1 (de)	1999-10-21
ATE270665T1 (de)	2004-07-15
EP1071670B1 (de)	2004-07-07
ITMI980818A1 (it)	1999-10-17
DE59909917D1 (de)	2004-08-12
MXPA00009474A (es)	2002-08-12
IT1300055B1 (it)	2000-04-05
JP4589531B2 (ja)	2010-12-01
WO1999054314A1 (de)	1999-10-28
EP1071670A1 (de)	2001-01-31
CA2322195C (en)	2008-02-26
US6255327B1 (en)	2001-07-03

Publication	Publication Date	Title
ES2224652T3 (es)	2005-03-01	Heterociclos de 5 anillos sustituidos con difenilo, procedimiento para su preparacion, asi como su empleo como medicamentos.
ES2256880T3 (es)	2006-07-16	Oxadiazoles, procedimiento para su preparacion, asi como su uso como medicamentos.
TWI837169B (zh)	2024-04-01	甲狀腺素受體β促效劑化合物
KR102650026B1 (ko)	2024-03-22	Irak 억제제로서의 헤테로아릴 화합물 및 이의 용도
DE60008372T2 (de)	2005-05-19	Pharmazeutisch aktive verbindungen
ES2270143T3 (es)	2007-04-01	Compuestos organicos como agentes para el tratamiento de condiciones mediadas por aldosterona.
ES2205166T3 (es)	2004-05-01	Derivados de isoquinolina y medicamento.
BRPI0806811A2 (pt)	2011-09-13	derivados de purina
ES2638398T3 (es)	2017-10-20	Derivados de pirazol oxadiazol como agonistas de S1P1
BR112014022271B1 (pt)	2021-09-21	Compostos com base em imidazo[1,2-b]piridazina, composições compreendendo-os, e usos dos mesmos
KR20110038671A (ko)	2011-04-14	아졸 화합물
KR20090033912A (ko)	2009-04-06	화학적 화합물
ES2235253T3 (es)	2005-07-01	Derivados novedosos de indol-2, 3-dion-3-oxima.
KR20210024574A (ko)	2021-03-05	세포 괴사 억제제 및 이의 제조 방법과 용도
IE912279A1 (en)	1992-01-01	1-indolylalkyl-4-(alkoxypyrimidinyl)piperazines
JPH04234857A (ja)	1992-08-24	３，５−ジ置換２−イソキサゾリンおよびイソキサゾール、それらの製法およびそれらを含有する薬学的組成物
EP0491218A1 (de)	1992-06-24	Benzodiazepinone
CN110709394B (zh)	2025-02-21	可用作alcat1抑制剂的化合物
JPH11513376A (ja)	1999-11-16	選択的β▲下３▼−アドレナリン作動剤
AU2021401834A1 (en)	2023-07-06	Boron containing pyrazole compounds, compositions comprising them, methods and uses thereof
KR101131378B1 (ko)	2012-04-04	치환된 디케토피페라진 및 옥시토신 길항제로서 그의 용도
US5232924A (en)	1993-08-03	Heterocyclic compound having serotonine 2-receptor antagonistic activity
SK42899A3 (en)	1999-08-06	3-alkoxyisoxazol-4-yl-substituted 2-amino carboxylic acid compounds
CN118922185A (zh)	2024-11-08	作为trpa1抑制剂的n3-取代的尿嘧啶化合物
OA11586A (en)	2004-07-26	FKBP inhibotors.